Rockport is a unique haven in any season. In the summer, we have lazy days in the hammock overlooking picturesque millpond, lying out on the beach, which is a two minute walk away, or using one of our many bikes to explore the island of Cape Ann, discovering views, shops or even swimming quaries.

There’s nothing like the aroma of a fireplace in the early fall. Some would claim that the best time to visit New England is when the leaves are singing in blaring colors and the many festivals and autumn celebrations give you an insight into this special part of the world.

Rockport comes alive in a different way over the holiday season, with ice sculptures lining the quaint streets, decorations overflowing the area, and carolers singing in the street. Seeing the snow drift over a white out over the village from the warmth of the cottage is a special kind of beauty and relaxation.

Come accept our invitation to stay in our cottage away from home.

When you arrive you’ll be greeted by a complimentary welcome basket with bread, eggs, and wine to start your time of peace. Every vacation rental has a working fireplace with stacks of wood, an ocean view, and bicycles. We also have beach chairs, linens, beach towels, icemakers, and a variety of family board games. We have grills for you to have a sizzling summer burger, as well as microwaves for the easier nights when you just feel like staying in and enjoying your TV with Cable, VHS, and DVD player. Each beach rental is also equipped with a CD player music system and wireless internet access, if you feel that you need to keep in contact with the real world. (We wouldn’t recommend it.)

Rockport, Massachusetts is perhaps one of the most famous art colonies in New England with Motif #1 being the premier artist subject when depicting a seacoast community. Being the closest point in the US to England, Rockport is steeped in history. It was settled in the 1600’s evidenced by old ship captain’s homes, pirate lore as well as many ancestral headstones throughout Rockport. Quaint shops line busy Bear Skin Neck with a host of art galleries to suit a wide spectrum of tastes. Homemade clam chowder and seafood specialties tantalize the palate while the beautiful vistas of Rockport’s natural rocky coast offer spectacular views. Wander the quaint lanes, enjoy front beach and relax in Cape Ann’s most photographed seaside village. Diversions are numerous – biking, swimming, diving, whale watching, sailing, boating or just relaxing. Rockport offers a wide range of activities for a fun filled vacation.

Take a stroll down Bearskin Neck, with a bevy of charming shops. Sample and savor the many seafood and authentic New England dishes in each restaurant hidden behind corners. Stop in at Roy Moore’s and grab a stuffed clam and shrimp cocktail. Sample the freshly made chowder at the Portside Chowder House, looking out over the Motif #1, a world famous red fishing shack which is one of the most photographed buildings in the area. Sample some home made taffy, browse the old world bookstore, housed in an old bank, or mosey around the many art galleries, maybe even buy a painting for your family as a souvenir and meory of your time in the land where time stands still. Take as unset sailboat tour around the coast aboard the “Appledoor” or treat yourself to an elegant dining experience on the rocks at the edge of the neck.

Bike around the island, touring the museums and gazing at the lighthouses. Take a while watch tour, or a deep fishing expedition.

The entire town of Rockport is a historical district, so all the building are as authentic as they were years ago. You won’t see over development here, but a picture perfect town the way all towns should be. With its beautiful architecture and seascape, it’s no wonder that it is a mecca for painters and artists.

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Hi! Welcome to Rockport Cottages!

Our family's ancestors came to Rockport, MA almost 400 years ago. We own a few cottages in town and rent them out for people looking for a taste of the artistic, ocean living life on the shores of Cape Ann.